JP2016523923A5 - - Google Patents
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- Publication number
- JP2016523923A5 JP2016523923A5 JP2016524308A JP2016524308A JP2016523923A5 JP 2016523923 A5 JP2016523923 A5 JP 2016523923A5 JP 2016524308 A JP2016524308 A JP 2016524308A JP 2016524308 A JP2016524308 A JP 2016524308A JP 2016523923 A5 JP2016523923 A5 JP 2016523923A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- pyridin
- chromeno
- chr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 102
- 229910052739 hydrogen Inorganic materials 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 41
- 229910052799 carbon Inorganic materials 0.000 claims 40
- 229910052731 fluorine Inorganic materials 0.000 claims 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 34
- 229910052801 chlorine Inorganic materials 0.000 claims 32
- 229910052794 bromium Inorganic materials 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 18
- 125000004452 carbocyclyl group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- -1 CN Inorganic materials 0.000 claims 7
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- BTRUIOQFDZOSHY-UHFFFAOYSA-N (2-chlorophenyl) N-(5H-chromeno[3,4-c]pyridin-8-yl)carbamate Chemical compound Clc1ccccc1OC(=O)Nc1ccc-2c(OCc3cnccc-23)c1 BTRUIOQFDZOSHY-UHFFFAOYSA-N 0.000 claims 1
- CGXOKVWAHQLXGW-LJQANCHMSA-N (2r)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-2-phenylacetamide Chemical compound C1([C@H](C(=O)NC=2C=C3C(C4=CC=NC=C4CO3)=CC=2)N)=CC=CC=C1 CGXOKVWAHQLXGW-LJQANCHMSA-N 0.000 claims 1
- RNAFKLYSCSXHPD-LJQANCHMSA-N (2r)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-3-phenylpropanamide Chemical compound C([C@@H](N)C(=O)NC=1C=C2C(C3=CC=NC=C3CO2)=CC=1)C1=CC=CC=C1 RNAFKLYSCSXHPD-LJQANCHMSA-N 0.000 claims 1
- YNMRRKYGGSQSFU-HXUWFJFHSA-N (2r)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-4-phenylbutanamide Chemical compound C([C@@H](N)C(=O)NC=1C=C2C(C3=CC=NC=C3CO2)=CC=1)CC1=CC=CC=C1 YNMRRKYGGSQSFU-HXUWFJFHSA-N 0.000 claims 1
- CGXOKVWAHQLXGW-IBGZPJMESA-N (2s)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-2-phenylacetamide Chemical compound C1([C@@H](C(=O)NC=2C=C3C(C4=CC=NC=C4CO3)=CC=2)N)=CC=CC=C1 CGXOKVWAHQLXGW-IBGZPJMESA-N 0.000 claims 1
- RNAFKLYSCSXHPD-IBGZPJMESA-N (2s)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NC=1C=C2C(C3=CC=NC=C3CO2)=CC=1)C1=CC=CC=C1 RNAFKLYSCSXHPD-IBGZPJMESA-N 0.000 claims 1
- YNMRRKYGGSQSFU-FQEVSTJZSA-N (2s)-2-amino-n-(5h-chromeno[3,4-c]pyridin-8-yl)-4-phenylbutanamide Chemical compound C([C@H](N)C(=O)NC=1C=C2C(C3=CC=NC=C3CO2)=CC=1)CC1=CC=CC=C1 YNMRRKYGGSQSFU-FQEVSTJZSA-N 0.000 claims 1
- WFVSUKUBLYVESU-UHFFFAOYSA-N (4-chlorophenyl) N-(5H-chromeno[3,4-c]pyridin-8-yl)carbamate Chemical compound Clc1ccc(OC(=O)Nc2ccc-3c(OCc4cnccc-34)c2)cc1 WFVSUKUBLYVESU-UHFFFAOYSA-N 0.000 claims 1
- IVCRVXIXNSGNHM-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(5H-chromeno[3,4-c]pyridin-8-yl)urea Chemical compound ClC1=C(C=CC=C1)NC(=O)NC=1C=CC2=C(C=1)OCC1=CN=CC=C12 IVCRVXIXNSGNHM-UHFFFAOYSA-N 0.000 claims 1
- KPRCWVQFESUUCZ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(5H-chromeno[3,4-c]pyridin-8-yl)urea Chemical compound ClC=1C=C(C=CC=1)NC(=O)NC=1C=CC2=C(C=1)OCC1=CN=CC=C12 KPRCWVQFESUUCZ-UHFFFAOYSA-N 0.000 claims 1
- DJTMFEHAIGRZPF-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-(2,2-diphenylethyl)urea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NCC(C1=CC=CC=C1)C1=CC=CC=C1 DJTMFEHAIGRZPF-UHFFFAOYSA-N 0.000 claims 1
- BHXYIFXMVVNQIC-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-(2-phenylethyl)urea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NCCC1=CC=CC=C1 BHXYIFXMVVNQIC-UHFFFAOYSA-N 0.000 claims 1
- BCDJWKMBPWSUHK-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-(5-methyl-3-phenyl-1,2-oxazol-4-yl)urea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NC=1C(=NOC=1C)C1=CC=CC=C1 BCDJWKMBPWSUHK-UHFFFAOYSA-N 0.000 claims 1
- QYLXRGPNVAGDCO-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-[2-(2-fluorophenyl)ethyl]urea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NCCC1=C(C=CC=C1)F QYLXRGPNVAGDCO-UHFFFAOYSA-N 0.000 claims 1
- WNMJUYWTRVMPEQ-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-[2-(4-methoxyphenyl)ethyl]urea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NCCC1=CC=C(C=C1)OC WNMJUYWTRVMPEQ-UHFFFAOYSA-N 0.000 claims 1
- QJHRHZPJPWCVKW-UHFFFAOYSA-N 1-(5H-chromeno[3,4-c]pyridin-8-yl)-3-pyridin-3-ylurea Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)NC=1C=NC=CC=1 QJHRHZPJPWCVKW-UHFFFAOYSA-N 0.000 claims 1
- HDBXFVKLXMNUSU-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yl)ethyl]-3-(5H-chromeno[3,4-c]pyridin-8-yl)urea Chemical compound O1COC2=C1C=CC(=C2)CCNC(=O)NC=1C=CC2=C(C=1)OCC1=CN=CC=C12 HDBXFVKLXMNUSU-UHFFFAOYSA-N 0.000 claims 1
- XIQJQAYYAFHPMW-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)ethyl]-3-(5H-chromeno[3,4-c]pyridin-8-yl)urea Chemical compound ClC=1C=C(CCNC(=O)NC=2C=CC3=C(C=2)OCC2=CN=CC=C23)C=CC=1 XIQJQAYYAFHPMW-UHFFFAOYSA-N 0.000 claims 1
- OJODPUIXUYWIRR-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-3-(5H-chromeno[3,4-c]pyridin-8-yl)urea Chemical compound ClC1=CC=C(CCNC(=O)NC=2C=CC3=C(C=2)OCC2=CN=CC=C23)C=C1 OJODPUIXUYWIRR-UHFFFAOYSA-N 0.000 claims 1
- UCZMYTXEMNXNDE-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-n-(5h-chromeno[3,4-c]pyridin-8-yl)acetamide Chemical compound ClC1=CC(F)=CC=C1CC(=O)NC1=CC=C2C3=CC=NC=C3COC2=C1 UCZMYTXEMNXNDE-UHFFFAOYSA-N 0.000 claims 1
- IEBXRPDWWLNACN-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(5h-chromeno[3,4-c]pyridin-8-yl)acetamide Chemical compound ClC1=CC=CC=C1CC(=O)NC1=CC=C2C3=CC=NC=C3COC2=C1 IEBXRPDWWLNACN-UHFFFAOYSA-N 0.000 claims 1
- AHNQVTCSJZEQDT-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(5h-chromeno[3,4-c]pyridin-8-yl)propanamide Chemical compound C=1C=C(C2=CC=NC=C2CO2)C2=CC=1NC(=O)C(C)C1=CC=CC=C1Cl AHNQVTCSJZEQDT-UHFFFAOYSA-N 0.000 claims 1
- KJIMWFQVOZMRGE-UHFFFAOYSA-N 2-(3-chlorophenyl)-N-(5H-chromeno[3,4-c]pyridin-8-yl)acetamide Chemical compound ClC1=CC=CC(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)=C1 KJIMWFQVOZMRGE-UHFFFAOYSA-N 0.000 claims 1
- SQHINJRHWDJXRM-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(5h-chromeno[3,4-c]pyridin-8-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1CC(=O)NC1=CC=C2C3=CC=NC=C3COC2=C1 SQHINJRHWDJXRM-UHFFFAOYSA-N 0.000 claims 1
- UJXHTHYNXFUCMC-UHFFFAOYSA-N 2-chloro-N-(5H-chromeno[3,4-c]pyridin-8-yl)benzamide Chemical compound ClC1=C(C(=O)NC=2C=CC3=C(C=2)OCC2=CN=CC=C23)C=CC=C1 UJXHTHYNXFUCMC-UHFFFAOYSA-N 0.000 claims 1
- BAXHOUDRVWMQHU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(5h-chromeno[3,4-c]pyridin-8-yl)propanamide Chemical compound C1=CC(Cl)=CC=C1CCC(=O)NC1=CC=C2C3=CC=NC=C3COC2=C1 BAXHOUDRVWMQHU-UHFFFAOYSA-N 0.000 claims 1
- ODGNSEPVILHVHZ-UHFFFAOYSA-N 3-acetamido-n-(5h-chromeno[3,4-c]pyridin-8-yl)benzamide Chemical compound CC(=O)NC1=CC=CC(C(=O)NC=2C=C3C(C4=CC=NC=C4CO3)=CC=2)=C1 ODGNSEPVILHVHZ-UHFFFAOYSA-N 0.000 claims 1
- BMZJYEWABRAFIN-UHFFFAOYSA-N 3-chloro-N-(5H-chromeno[3,4-c]pyridin-8-yl)benzamide Chemical compound ClC=1C=C(C(=O)NC=2C=CC3=C(C=2)OCC2=CN=CC=C23)C=CC=1 BMZJYEWABRAFIN-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- FPFXRLDBJQHNCD-UHFFFAOYSA-N C1=C2C(=CN=C1)COC=1C=C(C=CC12)NC(=O)N1CCC2=CC=CC=C12 Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC12)NC(=O)N1CCC2=CC=CC=C12 FPFXRLDBJQHNCD-UHFFFAOYSA-N 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000003890 Coronary Vasospasm Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- QAMVGKQJPNKSBN-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-1,3-thiazole-4-carboxamide Chemical compound S1C=NC(=C1)C(=O)NC=1C=CC2=C(C=1)OCC1=CN=CC=C12 QAMVGKQJPNKSBN-UHFFFAOYSA-N 0.000 claims 1
- IZKTTYVFUSSWDI-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-1-methylpyrrole-2-carboxamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)C=1N(C=CC=1)C IZKTTYVFUSSWDI-UHFFFAOYSA-N 0.000 claims 1
- OTGGVSYPRQDIIK-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-1H-benzimidazole-2-carboxamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)C1=NC2=C(N1)C=CC=C2 OTGGVSYPRQDIIK-UHFFFAOYSA-N 0.000 claims 1
- UOJNRGBOIIEOIV-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2,3-dihydro-1H-indene-2-carboxamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)C1CC2=CC=CC=C2C1 UOJNRGBOIIEOIV-UHFFFAOYSA-N 0.000 claims 1
- WUMAJJYZZADKLC-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(2,4-dichlorophenyl)acetamide Chemical compound ClC1=CC(Cl)=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=C1 WUMAJJYZZADKLC-UHFFFAOYSA-N 0.000 claims 1
- RBXFMDWQSNABLA-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(2,6-dichlorophenyl)acetamide Chemical compound ClC1=CC=CC(Cl)=C1CC(=O)NC1=CC=C2C(OCC3=C2C=CN=C3)=C1 RBXFMDWQSNABLA-UHFFFAOYSA-N 0.000 claims 1
- IDZWFKJRYUWVJY-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(2-methylphenyl)acetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC1=C(C=CC=C1)C)=O IDZWFKJRYUWVJY-UHFFFAOYSA-N 0.000 claims 1
- QIMNJRBKDAOQRQ-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(3,4-dichlorophenyl)acetamide Chemical compound ClC1=C(Cl)C=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=C1 QIMNJRBKDAOQRQ-UHFFFAOYSA-N 0.000 claims 1
- YUPGYPTZMKTTAP-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(3,4-dimethoxyphenyl)acetamide Chemical compound COC1=C(OC)C=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=C1 YUPGYPTZMKTTAP-UHFFFAOYSA-N 0.000 claims 1
- LEENXAASVZDRSM-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(3,5-difluorophenyl)acetamide Chemical compound FC1=CC(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)=CC(F)=C1 LEENXAASVZDRSM-UHFFFAOYSA-N 0.000 claims 1
- KEQMTZCSKXABDO-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(3,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC(OC)=CC(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)=C1 KEQMTZCSKXABDO-UHFFFAOYSA-N 0.000 claims 1
- QJSMBDVVWMAGSR-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(3,5-dimethylphenyl)acetamide Chemical compound CC1=CC(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)=CC(C)=C1 QJSMBDVVWMAGSR-UHFFFAOYSA-N 0.000 claims 1
- ORXMBZPQYXDQQX-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(4-fluoro-2-methylphenyl)acetamide Chemical compound CC1=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=CC(F)=C1 ORXMBZPQYXDQQX-UHFFFAOYSA-N 0.000 claims 1
- KHFOFGNTTRIJPF-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(4-fluorophenyl)acetamide Chemical compound FC1=CC=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=C1 KHFOFGNTTRIJPF-UHFFFAOYSA-N 0.000 claims 1
- ADUIKHXMDBYDAT-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(4-methylsulfanylphenyl)acetamide Chemical compound CSC1=CC=C(CC(=O)NC2=CC=C3C(OCC4=C3C=CN=C4)=C2)C=C1 ADUIKHXMDBYDAT-UHFFFAOYSA-N 0.000 claims 1
- DMYRIKHTFVQERX-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-(furan-2-yl)acetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC=1OC=CC=1)=O DMYRIKHTFVQERX-UHFFFAOYSA-N 0.000 claims 1
- NZBRLEXCQPTWND-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC1=CC(=CC=C1)C(F)(F)F)=O NZBRLEXCQPTWND-UHFFFAOYSA-N 0.000 claims 1
- LBKZJVWBRFTVES-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-[3-fluoro-5-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC1=CC(=CC(=C1)C(F)(F)F)F)=O LBKZJVWBRFTVES-UHFFFAOYSA-N 0.000 claims 1
- QUOZICDGQPLCLE-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-[4-(4-oxoquinazolin-3-yl)phenyl]acetamide Chemical compound O=C(CC1=CC=C(C=C1)N1C=NC2=CC=CC=C2C1=O)NC1=CC=C2C(OCC3=C2C=CN=C3)=C1 QUOZICDGQPLCLE-UHFFFAOYSA-N 0.000 claims 1
- WUJHGJQFQMQVLZ-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC1=CC=C(C=C1)C(F)(F)F)=O WUJHGJQFQMQVLZ-UHFFFAOYSA-N 0.000 claims 1
- YBOFPWRUNWZIOF-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-phenylacetamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(CC1=CC=CC=C1)=O YBOFPWRUNWZIOF-UHFFFAOYSA-N 0.000 claims 1
- VGQMWOUAEIQJGP-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-phenylbenzamide Chemical compound C=1(C(=CC=CC=1)C(=O)NC=1C=CC2=C(C=1)OCC1=CN=CC=C12)C1=CC=CC=C1 VGQMWOUAEIQJGP-UHFFFAOYSA-N 0.000 claims 1
- UAXCDKNHGLPZHN-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-pyrazin-2-ylacetamide Chemical compound O=C(CC1=CN=CC=N1)NC1=CC=C2C(OCC3=C2C=CN=C3)=C1 UAXCDKNHGLPZHN-UHFFFAOYSA-N 0.000 claims 1
- PJTJJTHPEOCXEG-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-pyridin-2-ylacetamide Chemical compound O=C(CC1=NC=CC=C1)NC1=CC=C2C(OCC3=C2C=CN=C3)=C1 PJTJJTHPEOCXEG-UHFFFAOYSA-N 0.000 claims 1
- FMXIZLYOEUVLNU-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-pyridin-3-yl-1,3-thiazole-4-carboxamide Chemical compound O=C(NC1=CC=C2C(OCC3=C2C=CN=C3)=C1)C1=CSC(=N1)C1=CC=CN=C1 FMXIZLYOEUVLNU-UHFFFAOYSA-N 0.000 claims 1
- AHXYVFIAXXXALD-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-pyridin-3-ylacetamide Chemical compound O=C(CC1=CC=CN=C1)NC1=CC=C2C(OCC3=C2C=CN=C3)=C1 AHXYVFIAXXXALD-UHFFFAOYSA-N 0.000 claims 1
- PFDHYCLVZXBAHX-UHFFFAOYSA-N N-(5H-chromeno[3,4-c]pyridin-8-yl)-2-pyridin-4-yl-1,3-thiazole-4-carboxamide Chemical compound C1=C2C(=CN=C1)COC=1C=C(C=CC=12)NC(=O)C=1N=C(SC=1)C1=CC=NC=C1 PFDHYCLVZXBAHX-UHFFFAOYSA-N 0.000 claims 1
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-
2014
- 2014-07-01 ES ES14740124.4T patent/ES2634628T3/es active Active
- 2014-07-01 EP EP14740124.4A patent/EP3016950B1/en not_active Not-in-force
- 2014-07-01 JP JP2016524308A patent/JP6522602B2/ja not_active Expired - Fee Related
- 2014-07-01 US US14/900,228 patent/US9663529B2/en active Active
- 2014-07-01 WO PCT/US2014/045008 patent/WO2015002926A1/en not_active Ceased
- 2014-07-01 CN CN201480047826.1A patent/CN105518005B/zh not_active Expired - Fee Related
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